1. Enjoy Maryland Blue Crabs at Tickler’s
Nothing says fall like feasting on Maryland blue crabs, and Tickler’s Crab Shack is an expert in freshly-caught seafood. With crabs being extra juicy and tender in the fall months, it’s the perfect time to indulge in seafood. Offering delicious sides, refreshing drinks, and decadent desserts, Tickler’s is the place to dine on Tilghman Island.
2. Tilghman Island Day
If you’re looking for a special fall event, Tilghman Island Day is a great choice. Offered annually around October, this small-town festival showcases the island’s rich heritage, vibrant culture, and a deep-rooted sense of community. Explore booths, sample cuisine, and even watch a boat race at this exciting event!
3. Live Music at Wylder Hotel
With a rotating schedule of events, this charming venue offers an array of musical genres to suit every taste. From soulful jazz to foot-tapping bluegrass, the weekend nights come alive with captivating performances that create an unforgettable ambiance.
4. S’mores by The Water
In the cooler months, nothing beats a cozy night by the Chesapeake Bay making s’mores. If you’re looking for the perfect setup, Wylder Hotel offers reservable bonfires by the water and a build-your-own s’mores package with your choice of wine. Sit back, toast marshmallows, and relax as the sun goes down.
5. Browse Local Shops
If you’re looking for the perfect way to spend an afternoon on Tilghman Island, we recommend exploring the local shops. Whether you’re browsing retro clothing at 2 Vintage Chicks, Chesapeake-inspired souvenirs at Tilghman Island Country Store, or fishing equipment at Fairbank Tackle, you will surely find the perfect gift for yourself or a friend.
6. Explore the Tilghman Watermen’s Museum
Immerse yourself in the rich maritime heritage of Tilghman Island at the Tilghman Watermen’s Maritime Museum.
This captivating museum pays homage to the island’s deep-rooted connection to the Chesapeake Bay and the traditional watermen’s way of life. Step into the exhibits that showcase historical artifacts, interactive displays, and informative narratives, offering a glimpse into the island’s fishing traditions, and more.
7. Attend Oysterfest at St.Michaels
Celebrate the beloved Chesapeake Bay delicacy at the annual OysterFest in St. Michaels. Located less than half an hour from Tilghman Island, this lively festival showcases the region’s rich oyster heritage with shucking contests, cooking demonstrations, live music, and, of course, a delectable abundance of freshly harvested oysters.
8. Relax in a Wood-Fired Sauna
When looking for things to do on Tilghman Island in the fall, nothing beats a cozy sauna session at Wylder Hotel. Guests of the hotel can enjoy ultimate relaxation and renewal from the wood-fired sauna, before slipping into bed for the evening for a peaceful sleep.
9. Tilghman Island Marina & Rentals Boat Tour
While less common than in the summer, Tilghman Island Marina & Rentals still offers water tours by request after August. These exclusive tours offer a unique opportunity to cruise along the picturesque waterways, surrounded by the serene beauty of Tilghman Island.
10. Run the Historic Drawbridge Half Marathon
Enjoy the scenery and community of Tilghman Island by participating in the annual Historic Drawbridge Half Marathon. Starting at Wylder Hotel, this half leads to the nearby town of St.Michaels and offers stunning views of the Chesapeake Bay. So lace up your shoes and get ready to enjoy the crisp fall air. .